Windows Server Architect

Phoenix Oversight Group LLC

9d • Remote

About The Position

The Windows Server Architect leads the design and technical direction for migrating a federal client's Windows Server estate, hosted in a FedRAMP-authorized AWS GovCloud environment, from Windows Server 2016 to Windows Server 2019 or 2025 ahead of end of support. As the Windows subject matter expert, the role owns the upgrade architecture end to end, from discovery through hardening, testing, and rollback, and guides DevSecOps, Security, and Test team members to deliver compliant, low-risk upgrades for mission-critical systems.

Requirements

• Bachelor’s degree and 7 years of relevant experience.
• An additional 2 years of experience (9 years total) with an Associate’s Degree in lieu of a Bachelor’s Degree.
• An additional 4 years of experience (11 years total) with a High School Diploma in lieu of a Bachelor’s Degree.
• Demonstrated experience leading Windows Server 2016 to 2019 or 2025 migrations in AWS (GovCloud experience preferred), including upgrade planning, testing, and rollback.
• Hands-on Windows Server OS hardening experience using federal and industry baselines.
• Experience integrating Windows servers with CyberArk for privileged access management.
• Deep Windows Server expertise (Active Directory, Group Policy, DNS, DHCP, PKI, patching, Remote Desktop Service) and strong PowerShell skills.
• Working knowledge of AWS services for Windows workloads (EC2, AMIs, VPC, Systems Manager, EBS snapshots).
• Experience with windows configuration management using Ansible (WMI, WinRM, PowerShell)
• Strong technical leadership and communication skills, with the ability to direct engineers and lead discussions with federal stakeholders.

Nice To Haves

• Microsoft Windows Server certification: Microsoft Certified: Windows Server Hybrid Administrator Associate, or the legacy MCSE: Core Infrastructure; equivalent hands-on experience may be considered.
• AWS certification (e.g., AWS Certified Solutions Architect – Associate or Professional).
• Experience with AWS Systems Manager (Automated system patching)
• Experience in managing software deployments through group policy.
• Experience with Microsoft Power BI, including Power BI Gateway administration.
• Experience configuring and hardening Windows IIS servers1.
• Experience supporting federal government systems with audit and vulnerability management.

Responsibilities

• Lead discovery of in-scope servers, cataloging roles, services, installed software, and dependencies.
• Design the upgrade approach for each server (in-place vs. rebuild), including AMI selection, EC2 sizing, and a phased, wave-based sequence with go/no-go checkpoints between waves.
• Define and validate OS hardening baselines (e.g., DISA STIGs, CIS Benchmarks, Active Directory Domain) and remediate outstanding security findings.
• Design secure administrative access, including RDP/jump server configuration and CyberArk privileged access integration.
• Plan certificate management and renewal, including certificate chain validation.
• Design Windows IIS-dependent workloads, such as Power BI Gateway servers.
• Partner with DevSecOps Engineers to automate Windows build standards and correct configuration drift.
• Partner with the Test Manager on each wave's test strategy, success criteria, and rollback procedures, and maintain the project Risk Register.
• Produce architecture artifacts (Implementation Blueprint, design documents, runbooks) in Confluence and Jira, ensuring alignment with the client's Technical Reference Model and audit, vulnerability requirements.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior